NOVEL 26-OXYGENATED PRODUCTS IN MICROBIAL-DEGRADATION OF ERGOSTEROL

被引：7

作者：

AMBRUS, G ^{[1
]}

JEKKEL, A ^{[1
]}

ILKOY, E ^{[1
]}

HORVATH, G ^{[1
]}

BOCSKEI, Z ^{[1
]}

机构：

[1] CHINOIN PHARMACEUT,BUDAPEST,HUNGARY

来源：

STEROIDS | 1995年 / 60卷 / 09期

关键词：

EGOSTEROL; MECHANISM OF MICROBIAL 26-OXIDATION;

D O I：

10.1016/0039-128X(95)00078-5

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In order to investigate the effect of the different stereochemistry of C-24 on the microbial C-26 oxidation of sterol side-chain the genetically modified Mycobacterium sp. BCS 396 strain was used to transform ergosterol. Ergosterol was converted to 3-oxo-4,22-ergostadien-26-oic acid methyl ester, 3-oxo-1,4,22-ergostatrien-26-oic acid methyl ester, and 3-oxo-1,4,22-ergostatrien-26-oic acid, the structures of which have been determined by IR, H-1 NMR, C-13 NMR, and mass spectroscopy. The X-ray structure of 3-oxo-4,22-ergostadien-26-oic acid methyl ester revealed that oxidation at C-26 of the ergostane side-chain generates a chiral center with S-configuration at C-25 as a result of chiral induction of the C-24 center.

引用

页码：626 / 629

页数：4

共 14 条

[1] HYDROGENATION OF UNSATURATED STEROID RING SYSTEMS WITH MYCOBACTERIUM PHLEI [J].